(1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate)

Base Information

• Chemical Name: (1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate)
• CAS No.: 128531-56-6
• Molecular Formula: C₂₉H₃₆N₂O₄
• Molecular Weight: 476.616
• Mol file: 128531-56-6.mol

Synonyms:

Chemical Property of (1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate)

There total 4 articles about (1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.0%

(1α,6α,8aα)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediol (128574-75-4) + p-N,N-dimethylaminobenzoic acid (619-84-1) → (1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate) (128531-56-6)

Guidance literature:

With tributyl-amine; 2-chloro-1-methylpyridinium p-toluenesulfonate; In dichloromethane; for 2h; Heating;

DOI:10.1055/s-1990-26786

Reference yield:

2-methylcyclohexane-1,3-dione (1193-55-1) → (1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate) (128531-56-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / hydroquinone / H₂O / 4 h / 70 - 80 °C

2: 28 g / D-(+)-proline / dimethylsulfoxide / 6 h / Ambient temperature

3: 52 percent / LiAlH₄ / diethyl ether / 1.) 0 deg C, 2.) room temperature, 3 h

4: 46 percent / tributylamine, 2-chloro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Heating

With lithium aluminium tetrahydride; tributyl-amine; 2-chloro-1-methylpyridinium p-toluenesulfonate; hydroquinone; D-Prolin; In diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1055/s-1990-26786

Reference yield:

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione (5073-65-4) → (1R,6R,8aR)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediyl bis(4-dimethylaminobenzoate) (128531-56-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 28 g / D-(+)-proline / dimethylsulfoxide / 6 h / Ambient temperature

2: 52 percent / LiAlH₄ / diethyl ether / 1.) 0 deg C, 2.) room temperature, 3 h

3: 46 percent / tributylamine, 2-chloro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Heating

With lithium aluminium tetrahydride; tributyl-amine; 2-chloro-1-methylpyridinium p-toluenesulfonate; D-Prolin; In diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1055/s-1990-26786

upstream raw materials:

(1α,6α,8aα)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-1,6-naphthalenediol

p-N,N-dimethylaminobenzoic acid

2-methylcyclohexane-1,3-dione

2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione